[AlphaScent]

I am out of anhydrous ether and want to get a reaction done tonight.  Can I use anhydrous THF in place of the ether for a organolithium coupling.  The reaction is attached.  THF is good for coordinating lithium and other organics, so I don't see why not.  It is a coupling between acrolein and 1-hexyne.

[Archer]

THF is, in my experience, superior to ether in many cases for solubility. Unfortunately this also includes water. You will need to tweek the work up to make sure that you don't lose much of your product in the aqueous phase. Use ether to extract and wash with brine to keep the THF in the organic phase and you should be fine. 

[AlphaScent]

Thanks Archer,

I figured as much with the water, but my company is strapped for cash right now and buying anhydrous ether is expensive.  A PhD colleague of mine said it should be fine for this coupling ans also for a reaction using methylmagnesium bromide displacing a tosylate.  The work-up for my grignard is pouring it into a 1:2 solution of 12 M ammonium hydroxide/ sat. ammonium chloride.  I should be ok.

[opsomath]

Aw yeah, I've run coupling reactions in THF lots of times. You should be fine. You can quench the reaction and rotovap off some of the THF first if you're worried about miscibility with water.